JPS62277482A - Primer composition - Google Patents
Primer compositionInfo
- Publication number
- JPS62277482A JPS62277482A JP12187286A JP12187286A JPS62277482A JP S62277482 A JPS62277482 A JP S62277482A JP 12187286 A JP12187286 A JP 12187286A JP 12187286 A JP12187286 A JP 12187286A JP S62277482 A JPS62277482 A JP S62277482A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- parts
- polyisocyanate compound
- primer
- primer composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 239000003822 epoxy resin Substances 0.000 claims abstract description 13
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 13
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 229920000459 Nitrile rubber Polymers 0.000 claims abstract description 10
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical group C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000001070 adhesive effect Effects 0.000 abstract description 8
- 239000007983 Tris buffer Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract description 3
- 238000004381 surface treatment Methods 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000002990 reinforced plastic Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- -1 polypropylene Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000272194 Ciconiiformes Species 0.000 description 1
- 241000178435 Eliokarmos dubius Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
３、発明の詳細な説明
産業上の利用分野
本発明はプライマー組成物、更（こ詳しくは、持１ｃＦ
ＲＰ（ガラス繊維強化プラスチック）の接着において適
用され、サンディングなどの表面前処理を必要とせず（
こ、良好な接着性を発現させることができるプライマー
組成物に関する。Detailed Description of the Invention 3. Detailed Description of the Invention Field of Industrial Application The present invention provides a primer composition,
It is applied to bonding RP (glass fiber reinforced plastic) and does not require surface pretreatment such as sanding (
This invention relates to a primer composition that can exhibit good adhesion.
Ｆ４Ｐは各種構造体のパーツ（成形品、積層品）などに
用いられており、その需要が急激に伸びているが、特≦
こＦＲＰ同士の接着は極めて困難である。接着剤として
、一般にＦＲＰの種類に応じウレタン系接着剤やエポキ
シ系接着剤が使用されているが、ウレタン系接着剤の方
が柔軟で弾力性のある接着層を形成する反面、十分な接
着性を得る番こは、先ずＦＲＰ面にサンディングなどの
機械的な表面処理を行い１次いでプライマーを塗布して
おくことが必要である。この場合のプライマーとして、
従来よりポリイソシアネート化合物の溶剤希釈溶液、あ
るいはこれに塩素化ゴムや塩素化ポリプロピレンを少量
配合したものが採用されている。しかしながら、サンデ
ィングなどの機械的処理は作業工程を複雑化するため、
これらの処理を必要としないプライマーの出現が望まれ
ている。F4P is used for parts of various structures (molded products, laminated products), etc., and its demand is rapidly increasing.
It is extremely difficult to bond these FRP pieces together. Urethane adhesives and epoxy adhesives are generally used as adhesives depending on the type of FRP, but while urethane adhesives form a more flexible and elastic adhesive layer, they do not have sufficient adhesive properties. To obtain this, it is necessary to first perform mechanical surface treatment such as sanding on the FRP surface, and then apply a primer. As a primer in this case,
Conventionally, a dilute solution of a polyisocyanate compound in a solvent, or a solution containing a small amount of chlorinated rubber or chlorinated polypropylene has been used. However, mechanical processing such as sanding complicates the work process, so
It is desired that a primer that does not require these treatments be developed.
本発明者らは、かかる要望に適合するプライマーについ
て鋭意検討を進めた結果、プライマー主成分のポリイソ
シアネート化合物に、特定のゴム成分で変性したエポキ
シ樹脂を配合すれば、所期目的のプライマーが得られる
ことを見出し、本発明を完成するに至った。As a result of intensive research into primers that meet these demands, the present inventors found that by blending an epoxy resin modified with a specific rubber component into the polyisocyanate compound that is the main component of the primer, the desired primer could be obtained. The present invention was completed based on the discovery that the present invention is possible.
発明の構成と効果
すなわち、本発明は、ポリイソシアネート化合物および
ブタジェンアクリロニトリル共重合体で変性したエポキ
シ樹脂（以下、変性エポキシ樹脂と称す）から成ること
を特徴とするプライマー組成物を提供するものである。Structure and Effects of the Invention Specifically, the present invention provides a primer composition comprising an epoxy resin modified with a polyisocyanate compound and a butadiene acrylonitrile copolymer (hereinafter referred to as modified epoxy resin). be.
本発明におけるポリイソシアネート化合物としては、た
とえばヘキサメチレンジインシアネート。Examples of the polyisocyanate compound in the present invention include hexamethylene diinsyanate.
２、２．４−トリメチルへキサメチレンジイソシアネー
ト、リジンメチルエステルジイソシアネートなどの脂肪
族ポリイソシアネート類、水添ジフェニルメタンジイン
シアネート、インホロンジイソシアネート、水添トリレ
ンジイソシアネートなどの脂環式ポリイソノアネート類
、トリレンジイソシア不−）（ＴＤＩ）、 ジフェニ
ルメタンジイソシアネート、（ＭＤ Ｉ ） 、 ナ
フチレンジイソシアネート、キシリレンジイソシアネー
ト、トリフェニルメタントリイソシアネート、トリス（
４−フェニルイソシアネート）チオホスフェートなどの
芳香挨ポリイソシアネート類が挙げられ、これらの１種
または２種以上の混合物を使用に供する。Aliphatic polyisocyanates such as 2,2,4-trimethylhexamethylene diisocyanate and lysine methyl ester diisocyanate, alicyclic polyisonoanates such as hydrogenated diphenylmethane diisocyanate, inphorone diisocyanate, and hydrogenated tolylene diisocyanate; Tolylene diisocyanate (TDI), diphenylmethane diisocyanate, (MDI), naphthylene diisocyanate, xylylene diisocyanate, triphenylmethane triisocyanate, tris(
Examples include aromatic polyisocyanates such as 4-phenylisocyanate) thiophosphate, and one or a mixture of two or more of these may be used.
本発明における変性エポキシ樹脂は、通常のエポキシ樹
脂（グリシジルエーテル型、グリシジルエステル型、グ
リシジルアミン型、線状脂肪族エポキサイド型、脂環族
エポキサイド型など）に、エポキシ基と反応しうる官能
基（カルボキシル基、アミン基）を末端に有するブタジ
ェンアクリロニトリル共重合体を反応させることにより
得られる。反応は通常、エポキシ樹脂１００部（重量部
、以下同様）に対してブタジェンアクリロニトリル共重
合体５０〜２００部の割合で選定し、１２０〜１４０℃
、３〜６時間の条件で行なえばよい。The modified epoxy resin in the present invention is a normal epoxy resin (glycidyl ether type, glycidyl ester type, glycidyl amine type, linear aliphatic epoxide type, alicyclic epoxide type, etc.) with a functional group that can react with an epoxy group. It is obtained by reacting a butadiene-acrylonitrile copolymer having a terminal group (carboxyl group, amine group). The reaction is usually carried out at a temperature of 120 to 140°C, with a ratio of 50 to 200 parts of the butadiene acrylonitrile copolymer to 100 parts (by weight, the same applies hereinafter) of the epoxy resin.
, for 3 to 6 hours.
上記エポキシ基反応性官能基を有するブタジェンアクリ
ロニトリル共重合体としては、たとえば式：
（式中、ｘ” ｉｔ３〜１０．ｙ’ ｉｔｌ〜５および
ｎｌは８〜２０）
のカルボキシル基末端ブタジェ〕／アクリロニトリル共
重合体、または式：
（式中、ｘ２は３〜１０、ｙ２は１〜５およびｎ２は８
〜２０）
のアミン基末端ブタジェンアクリロニトリル共骸合体が
挙げられ、これらは宇部興産（株）から商■
品名ｒ Ｈｙｃａｒ ＣＴ Ｂ Ｎ Ｊ 、 ［Ｈｙ
ｃａｒ■ＡＴＢＮＪで入手することができる。The butadiene-acrylonitrile copolymer having the above-mentioned epoxy group-reactive functional group is, for example, a carboxyl-terminated butadiene copolymer of the formula: Acrylonitrile copolymer, or formula: (where x2 is 3 to 10, y2 is 1 to 5, and n2 is 8
~20) amine group-terminated butadiene acrylonitrile copolymerizers are mentioned, and these are commercially available from Ube Industries, Ltd.
It can be obtained from car■ATBNJ.
かかる変性エポキシ樹脂の配合量は通常、ポリイソシア
ネート化合物１００部に対して５〜５０部、好ましくは
１０〜３０部の範囲で選定すればよい。５部未満である
と、接着性の低下、また５゜部を越えると、プライマー
強度が低下する傾向にある。The amount of the modified epoxy resin to be blended is usually 5 to 50 parts, preferably 10 to 30 parts, based on 100 parts of the polyisocyanate compound. If the amount is less than 5 parts, the adhesiveness tends to decrease, and if it exceeds 5 parts, the primer strength tends to decrease.
本発明に係るプライマー組成物は、上記所定割合のポリ
イソシアネート化合物と変性エポキシ樹脂を配合し、こ
れらを要すれば適当な有機溶剤（酢酸エチル、メチルエ
チルケトン、酢酸ブチル、トルエン、キシレン、メチレ
ンクロリドなど）で不揮発分が５〜４０％（重量％、以
下同様）となるように希釈Ｎ８整した糸で構成される。The primer composition according to the present invention contains a polyisocyanate compound and a modified epoxy resin in the above-mentioned predetermined proportions, and if necessary, a suitable organic solvent (ethyl acetate, methyl ethyl ketone, butyl acetate, toluene, xylene, methylene chloride, etc.). The yarn is diluted to N8 so that the nonvolatile content is 5 to 40% (by weight, the same applies hereinafter).
本発明組成物は、主にＦＲＦ’用ウレタウレタン系接着
剤イマーとして適用され、従来のサンディング処理を省
略しても、所望の接着性を発現させることが可能となる
。また、かかる用途以外にも、種々のポリオレフィン材
料、合成樹脂フィルム、合成樹脂皮幕等への接着プライ
マー、あるいは塗料プライマーとして利用することがで
きる。The composition of the present invention is mainly applied as a urethane adhesive immer for FRF', and it is possible to develop desired adhesiveness even if the conventional sanding treatment is omitted. In addition to such uses, it can also be used as an adhesive primer for various polyolefin materials, synthetic resin films, synthetic resin coatings, etc., or as a paint primer.
次に実施例を挙げて本発明をより具体的に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施１３’ｌＪ １〜５
トリス（４−フエニルインシアネートンチオホスフエー
ト（住友バイエルウレタン社製、デスモジュールＲＦ、
不揮発２０％）１００部に各種変性エポキシ樹脂１〜１
０部を配合し、これを酢酸エチルで不揮発分２０％に希
釈調整してプライマー組成物を得る。かかる成分配合を
下記表１に示す。Implementation 13'lJ 1-5 Tris(4-phenylincyanatone thiophosphate (manufactured by Sumitomo Bayer Urethane, Desmodur RF,
100 parts of non-volatile 20%) and 1 to 1 of various modified epoxy resins
0 parts, and diluted with ethyl acetate to a non-volatile content of 20% to obtain a primer composition. The composition of such ingredients is shown in Table 1 below.
比較例１
上記デスモジュールＲＦをそのままプライマーとして使
用する。Comparative Example 1 The above desmodule RF is used as it is as a primer.
試験方法
２枚のＦＲＰ板の表面を溶剤で脱脂し、これに各実施例
または比較例のプライマーを塗布し、次いで二液型ウレ
タン系接着剤（サンスター技研（株）製、ペンギンンー
ル１９８０）を塗布した後、両ＦＲＰ板を貼り合せて２
０℃で３日間放置する。Test method The surfaces of two FRP boards were degreased with a solvent, the primer of each example or comparative example was applied thereto, and then a two-component urethane adhesive (manufactured by Sunstar Giken Co., Ltd., Penguin Rule 1980) was applied. After applying, paste both FRP boards together and
Leave at 0°C for 3 days.
硬ｆヒ接着したＦにＰ板をはくり試験に供し、接着性を
評価する。結果を表１に示す。A P plate is peeled off from F which has been hard-bonded, and the adhesion is evaluated. The results are shown in Table 1.
表１
注■）エポキシ樹脂（シェル化学社製、エピコート８２
８）１００部とカルボキシル基末端ブタジェンアクリロ
ニトリル共重合体（宇部興産（株）製、ＣＴＢＮ１３０
０Ｘ３１、分子量３５００、アクリロニトリル量１０％
）１００部を、１２０℃×５時間で反応させたもの。Table 1 Note ■) Epoxy resin (manufactured by Shell Chemical Co., Ltd., Epicoat 82
8) 100 parts and carboxyl group-terminated butadiene acrylonitrile copolymer (manufactured by Ube Industries, Ltd., CTBN130)
0X31, molecular weight 3500, acrylonitrile amount 10%
) was reacted at 120°C for 5 hours.
■）エピコート８２８（１００部）とカルボキシル基末
端ブタジェンアクリロニトリル共重合体（宇部興産（株
）製、ＣＴＢＮ１３００Ｘ１３、分子量３５００ 、ア
クリロニトリル量２７％）１００部を、１２０℃×５時
間で反応させたもの。■) Epicote 828 (100 parts) and 100 parts of carboxyl-terminated butadiene acrylonitrile copolymer (manufactured by Ube Industries, Ltd., CTBN1300X13, molecular weight 3500, acrylonitrile content 27%) were reacted at 120°C for 5 hours. .
■）エピコート８２８（１００部）とアミン基末端ブタ
ジェンアクリロニトリル共重合体（宇部興産（株）製、
ＡＴＢＮＩ３００ＸＩ ６、分”［Ｌ３ｓｏｏ、アクリ
ロニトリル量１６．５％）１００部を５０℃×４８時間
で反応させたもの。■) Epicoat 828 (100 parts) and amine group-terminated butadiene acrylonitrile copolymer (manufactured by Ube Industries, Ltd.,
100 parts of ATBNI300XI 6 minutes" [L3soo, acrylonitrile amount 16.5%] was reacted at 50°C for 48 hours.
■）ｏ：凝集破壊、×：界面破壊。■) o: cohesive failure, ×: interfacial failure.
Claims (1)
ロニトリル共重合体で変性したエポキシ樹脂から成るこ
とを特徴とするプライマー組成物。 ２、ポリイソシアネート化合物１００重量部に対して変
性エポキシ樹脂５〜５０重量部を配合した前記第１項記
載の組成物。[Scope of Claims] 1. A primer composition comprising an epoxy resin modified with a polyisocyanate compound and a butadiene acrylonitrile copolymer. 2. The composition according to item 1 above, wherein 5 to 50 parts by weight of a modified epoxy resin is blended with 100 parts by weight of the polyisocyanate compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12187286A JPS62277482A (en) | 1986-05-26 | 1986-05-26 | Primer composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12187286A JPS62277482A (en) | 1986-05-26 | 1986-05-26 | Primer composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62277482A true JPS62277482A (en) | 1987-12-02 |
Family
ID=14822014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12187286A Pending JPS62277482A (en) | 1986-05-26 | 1986-05-26 | Primer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62277482A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001094493A3 (en) * | 2000-06-06 | 2002-06-20 | Dow Global Technologies Inc | Epoxy based reinforcing patches with improved adhesion to oily metal surfaces |
-
1986
- 1986-05-26 JP JP12187286A patent/JPS62277482A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001094493A3 (en) * | 2000-06-06 | 2002-06-20 | Dow Global Technologies Inc | Epoxy based reinforcing patches with improved adhesion to oily metal surfaces |
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